DD299650A5 - 4-substituierte 17 beta-(cyclopropylamino)-androst-5-en-3beta-ole und verwandte verbindungen, verfahren zu ihrer herstellung und ihre verwendung - Google Patents
4-substituierte 17 beta-(cyclopropylamino)-androst-5-en-3beta-ole und verwandte verbindungen, verfahren zu ihrer herstellung und ihre verwendung Download PDFInfo
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- DD299650A5 DD299650A5 DD90343476A DD34347690A DD299650A5 DD 299650 A5 DD299650 A5 DD 299650A5 DD 90343476 A DD90343476 A DD 90343476A DD 34347690 A DD34347690 A DD 34347690A DD 299650 A5 DD299650 A5 DD 299650A5
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- 238000000034 method Methods 0.000 title claims description 13
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- 239000000203 mixture Substances 0.000 claims description 12
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- 229910052717 sulfur Inorganic materials 0.000 description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 3
- VMMCAVYAQKEQOU-QWJDIHMQSA-N (3s,8r,9s,10r,13s,14s)-n-cyclopropyl-4,4-difluoro-10,13-dimethyl-3-(oxan-2-yloxy)-2,3,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-imine Chemical compound O([C@@H]1C(F)(F)C2=CC[C@@H]3[C@@H]([C@]2(CC1)C)CC[C@]1([C@H]3CCC1=NC1CC1)C)C1CCCCO1 VMMCAVYAQKEQOU-QWJDIHMQSA-N 0.000 description 2
- OWIQKHSHMWDZCY-OAUGPMCWSA-N (3s,8r,9s,10r,13s,14s,17s)-17-[cyclopropyl(methyl)amino]-4,4-difluoro-10,13-dimethyl-1,2,3,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ol Chemical compound CN([C@@H]1[C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)C(F)(F)C4=CC[C@H]3[C@@H]2CC1)C)C1CC1 OWIQKHSHMWDZCY-OAUGPMCWSA-N 0.000 description 2
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- 206010047486 Virilism Diseases 0.000 description 1
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- FMGSKLZLMKYGDP-USOAJAOKSA-N dehydroepiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-USOAJAOKSA-N 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 229960005309 estradiol Drugs 0.000 description 1
- 229930182833 estradiol Natural products 0.000 description 1
- 229960003399 estrone Drugs 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000003676 hair loss Effects 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N hydroxymaleic acid group Chemical group O/C(/C(=O)O)=C/C(=O)O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- JKWKFBUUNGGYBP-UHFFFAOYSA-N n-cyclopropylcyclopropanamine Chemical compound C1CC1NC1CC1 JKWKFBUUNGGYBP-UHFFFAOYSA-N 0.000 description 1
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229960002847 prasterone Drugs 0.000 description 1
- 229960000249 pregnenolone Drugs 0.000 description 1
- OZZAYJQNMKMUSD-DMISRAGPSA-N pregnenolone succinate Chemical compound C1C=C2C[C@@H](OC(=O)CCC(O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 OZZAYJQNMKMUSD-DMISRAGPSA-N 0.000 description 1
- 229960003387 progesterone Drugs 0.000 description 1
- 239000000186 progesterone Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000009901 transfer hydrogenation reaction Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/394,025 US4966898A (en) | 1989-08-15 | 1989-08-15 | 4-substituted 17β-(cyclopropylamino)androst-5-en-3β-ol and related compounds useful as C17-20 lyase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD299650A5 true DD299650A5 (de) | 1992-04-30 |
Family
ID=23557240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD90343476A DD299650A5 (de) | 1989-08-15 | 1990-08-15 | 4-substituierte 17 beta-(cyclopropylamino)-androst-5-en-3beta-ole und verwandte verbindungen, verfahren zu ihrer herstellung und ihre verwendung |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4966898A (fi) |
| EP (1) | EP0413270B1 (fi) |
| JP (1) | JP2879703B2 (fi) |
| KR (1) | KR910004649A (fi) |
| CN (1) | CN1050196A (fi) |
| AT (1) | ATE137761T1 (fi) |
| AU (1) | AU628209B2 (fi) |
| CA (1) | CA2023012C (fi) |
| DD (1) | DD299650A5 (fi) |
| DE (1) | DE69026881T2 (fi) |
| ES (1) | ES2088928T3 (fi) |
| FI (1) | FI95804C (fi) |
| HU (1) | HUT55029A (fi) |
| IE (1) | IE72516B1 (fi) |
| IL (1) | IL95358A (fi) |
| NO (1) | NO903564L (fi) |
| NZ (1) | NZ234856A (fi) |
| PH (1) | PH27098A (fi) |
| PT (1) | PT94993B (fi) |
| ZA (1) | ZA906308B (fi) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4966897A (en) * | 1989-08-15 | 1990-10-30 | Merrell Dow Pharmaceuticals Inc. | 4-substituted 17β-(cyclopropyloxy)androst-5-en-3β-ol and related compounds useful as C17-20 lyase inhibitors |
| GB2265624B (en) * | 1992-03-31 | 1995-04-19 | British Tech Group | 17-substituted steroids useful in cancer treatment |
| US5604213A (en) * | 1992-03-31 | 1997-02-18 | British Technology Group Limited | 17-substituted steroids useful in cancer treatment |
| TW369521B (en) * | 1993-09-17 | 1999-09-11 | Smithkline Beecham Corp | Androstenone derivative |
| US5541322A (en) * | 1994-10-14 | 1996-07-30 | Glaxo Wellcome Inc. | Synthesis of 6-azaandrostenones |
| US6365597B1 (en) | 1996-02-14 | 2002-04-02 | Aventis Pharmaceuticals Inc. | 4-aza steroids |
| JP4954425B2 (ja) * | 2000-06-09 | 2012-06-13 | メリアル・リミテツド | 農薬化合物の調製方法 |
| ES2260303T3 (es) | 2000-11-17 | 2006-11-01 | Takeda Pharmaceutical Company Limited | Derivados de imidazol, metodo para su produccion, y su uso. |
| US6960586B2 (en) | 2000-11-20 | 2005-11-01 | Takeda Pharmaceutical Company Limited | Imidazole derivatives, process for their preparation and their use |
| US7067537B2 (en) | 2000-12-08 | 2006-06-27 | Takeda Pharmaceutical Company Limited | Substituted thiazole derivatives bearing 3-pyridyl groups, process for preparing the same and use thereof |
| US20080051380A1 (en) | 2006-08-25 | 2008-02-28 | Auerbach Alan H | Methods and compositions for treating cancer |
| ES2475945T3 (es) | 2009-06-26 | 2014-07-11 | Novartis Ag | Derivados imidazolidin-2 -ona 1,3-disustituida como inhibidores de CYP 17 |
| JP2011098893A (ja) * | 2009-11-04 | 2011-05-19 | Sumitomo Chemical Co Ltd | テストステロンの生合成を抑制するための化合物の使用およびその化合物 |
| AU2011285724B2 (en) | 2010-08-04 | 2015-01-22 | Pellficure Pharmaceuticals, Inc. | Combination therapy for the treatment of prostate carcinoma |
| CN103108871B (zh) | 2010-09-16 | 2014-09-10 | 诺华股份有限公司 | 17α-羟化酶/C17,20-裂合酶抑制剂 |
| BR112013027395A2 (pt) | 2011-04-28 | 2017-01-17 | Novartis Ag | inibidores de 17alfa-hidroxilase/c17,20-liase |
| WO2014158875A1 (en) | 2013-03-14 | 2014-10-02 | Pellficure Pharmaceuticals Inc. | Novel therapy for prostate carcinoma |
| AU2015314772B2 (en) | 2014-09-12 | 2020-02-27 | Pellficure Pharmaceuticals, Inc. | Compositions and methods for treatment of prostate carcinoma |
| MX2019001224A (es) | 2016-07-29 | 2019-06-03 | Janssen Pharmaceutica Nv | Metodos para tratar el cancer de prostata. |
| CA3044812A1 (en) | 2016-10-24 | 2018-05-03 | Pellficure Pharmaceuticals Inc. | Pharmaceutical compositions of 5-hydroxy-2-methylnaphthalene-1,4-dione |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3107254A (en) * | 1960-10-05 | 1963-10-15 | Upjohn Co | 17beta-dialkylamino-17-cyanosteroids and their 17alpha-alkyl, alkylene and alkyne derivatives |
| US3097200A (en) * | 1962-01-03 | 1963-07-09 | Syntex Corp | 17-aminoandrostanes |
| NL302932A (fi) * | 1962-12-31 | |||
| CA1326234C (en) * | 1987-04-22 | 1994-01-18 | Michael R. Angelastro | 17.beta.-(cyclopropylamino)androst-5-en-3.beta.-ol and related compoundsuseful as_c__-__ lyase inhibitors |
| US4966897A (en) * | 1989-08-15 | 1990-10-30 | Merrell Dow Pharmaceuticals Inc. | 4-substituted 17β-(cyclopropyloxy)androst-5-en-3β-ol and related compounds useful as C17-20 lyase inhibitors |
-
1989
- 1989-08-15 US US07/394,025 patent/US4966898A/en not_active Expired - Fee Related
-
1990
- 1990-08-09 AU AU60877/90A patent/AU628209B2/en not_active Ceased
- 1990-08-09 ZA ZA906308A patent/ZA906308B/xx unknown
- 1990-08-09 JP JP2209389A patent/JP2879703B2/ja not_active Expired - Fee Related
- 1990-08-09 CA CA002023012A patent/CA2023012C/en not_active Expired - Fee Related
- 1990-08-10 EP EP90115391A patent/EP0413270B1/en not_active Expired - Lifetime
- 1990-08-10 DE DE69026881T patent/DE69026881T2/de not_active Expired - Fee Related
- 1990-08-10 NZ NZ234856A patent/NZ234856A/en unknown
- 1990-08-10 AT AT90115391T patent/ATE137761T1/de not_active IP Right Cessation
- 1990-08-10 ES ES90115391T patent/ES2088928T3/es not_active Expired - Lifetime
- 1990-08-13 IL IL9535890A patent/IL95358A/en not_active IP Right Cessation
- 1990-08-14 NO NO90903564A patent/NO903564L/no unknown
- 1990-08-14 PT PT94993A patent/PT94993B/pt not_active IP Right Cessation
- 1990-08-14 KR KR1019900012533A patent/KR910004649A/ko not_active Application Discontinuation
- 1990-08-14 IE IE294290A patent/IE72516B1/en not_active IP Right Cessation
- 1990-08-14 HU HU905004A patent/HUT55029A/hu unknown
- 1990-08-15 FI FI904035A patent/FI95804C/fi not_active IP Right Cessation
- 1990-08-15 PH PH41034A patent/PH27098A/en unknown
- 1990-08-15 DD DD90343476A patent/DD299650A5/de unknown
- 1990-08-15 CN CN90107580A patent/CN1050196A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IE902942A1 (en) | 1991-02-27 |
| IL95358A0 (en) | 1991-06-30 |
| ATE137761T1 (de) | 1996-05-15 |
| PH27098A (en) | 1993-02-26 |
| NZ234856A (en) | 1992-08-26 |
| HU905004D0 (en) | 1991-01-28 |
| DE69026881D1 (de) | 1996-06-13 |
| AU628209B2 (en) | 1992-09-10 |
| EP0413270A2 (en) | 1991-02-20 |
| KR910004649A (ko) | 1991-03-29 |
| FI904035A0 (fi) | 1990-08-15 |
| NO903564L (no) | 1991-02-18 |
| CA2023012A1 (en) | 1991-02-16 |
| IL95358A (en) | 1995-03-30 |
| ZA906308B (en) | 1991-06-26 |
| PT94993A (pt) | 1991-04-18 |
| FI95804C (fi) | 1996-03-25 |
| FI95804B (fi) | 1995-12-15 |
| ES2088928T3 (es) | 1996-10-01 |
| CN1050196A (zh) | 1991-03-27 |
| DE69026881T2 (de) | 1996-09-12 |
| HUT55029A (en) | 1991-04-29 |
| NO903564D0 (no) | 1990-08-14 |
| CA2023012C (en) | 2001-07-03 |
| AU6087790A (en) | 1991-02-21 |
| JPH0383998A (ja) | 1991-04-09 |
| EP0413270A3 (en) | 1992-05-20 |
| US4966898A (en) | 1990-10-30 |
| PT94993B (pt) | 1997-07-31 |
| EP0413270B1 (en) | 1996-05-08 |
| IE72516B1 (en) | 1997-04-23 |
| JP2879703B2 (ja) | 1999-04-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| IF04 | In force in the year 2004 |
Expiry date: 20100816 |